Azodyestuffs and process of making same



Patented Apr. 24, 1928.

UNITED STATES PATENT OFFICE.

AUGUST LEOPOLD LASKA. AND ARTHUR Z ITSCHER, 0F OFFENBACHY-ON-THE-MAIN, GERMANY, ASSIGNORS TO I. G. FARBENINDUSTRIE AKTIENGESELLSCHAFT, OI

IRANKFOBT, GERMANY.

AZODYESTUFFS AND PROCESS Of MAKING SAME.

Io Drawing. Application filed September 10, 1925,

Our invention relates to new azodyestufis and a process of making same, said dyestufis having probably the general formula:

N N X CO-NH-Aryl in which formula X represents the residue of a pseudoaziminobody of the general formula:

n is either 1 or 2, that is, an integer eater than zero and smaller than 3, whic dyestuffs are when dry scarlet red to black violet powders, soluble in sulfuric acid to a red, violet to blue solution, yielding on reduction with stannous chloride an aminopseudoaziminobody and an arylid of 1-amino-2-hydroxy-3-naphthoic acid, which d estufl's are adapted for the production of valuable color lakes, when mixed with the usual substrata,

and d e, when produced on the fiber, the

Serial No. 55,628, and in Germany October 8, 1824.

aminogroup, the combination with the arylids of 2.3-l1ydroxynaphthoic acid is executed in equimolecular proportions; a pseudoaziminobody, containing two aminogroups, is combined with two molecular proportions of the ar lid.

The aminopseu oazimins may be obtained according to the known processes by reducing nitrosubstituted pseudoazimins or accordin to the process of Schmidt and Hagen ticker, which involves treating orthoaminoazodyestufis with cupric-oxide-ammonium salts, details of said process being described in Beric hte der Deutschen Chemischen Gesellschaft, volume 54, page 2191, and in the German Letters Patent No. 338,926.

Among the compounds of this kind, not described hitherto, the following may be mentioned:

2-(2 aminophenyl) pseudoazimino-oc-B- naphthalene, crystallizing from alcohol of 80 p. c. as feebly colored granules, melting at 120 C. (not corrected),

2 (37- aminophenyl) pseudoazimino a B- naphthalene, crystallizing from a mixture of xylene and ligroin as almost colorless granules, melting at 160 C. (not corrected), 2 (4'- aminophenyl) pseudoazimino a B- naph'thalene crystallizing from xylene as 'almost colorless granules, melting at 203205 C. (not corrected),

2- (3'-amino-4-methyl-phenyl) -pseudoazimino-a-B-naphthalene, obtained from a mixture of xylene and ligroin as colorless scales, melting at 1721 73 G. (not corrected),

2-(3 amino -4-methoXy-phenyl) pseudoazimino-a-B-naphthalene, crystallizing from xylene as feebly yellowish soft needles, melting at 185 C. (not corrected),

Reissue) 2- (2-amino-4'-methylphenyl) pseudoazimino-a-B-naphthalene, crystallizing from a mixture of alcoh l and pyridine as lemonyellow soft needles, melting at l37136 C. (not corrected),

2 (2 amino 4' chlorophenyl) -pseudoazimino-a-B-naphthalene, crystallizing from xylene as feebly yellowish glassy scales, melting at 192 C. (not corrected).

As azocomponents for the process all the arylids of 2.3-hydroxynaphtholic acid may be used, such as for example the anilid, toluidids, anisidids and phenetidids, ozand ,8- naphthalid, arylids, chlorosubstituted in the arylido residue, the bis-2.3-hydroxynaphthoyl-arylene-diamins and so on.

The following examples illustrate the invention.

Ewample 1.

Cotton yarn, well boiled and dried, is impregnated with a solution of dark garnet red shades of'a very good fastness to kier boiling are obtained.

In the first-mentioned case, the bluish red dyestufl formed on the fiber probably has the following formula:

In the last-mentioned case, the dark garnet red dyestuflf formed on the fiber probably 45 has the following formula:

Ewample Q.

In the same manner, as described in Example 1, cotton yarn is impregnated with a solution of 4 gr. of B-naphthalid of 2.3-hydroxynaphthoic acid per liter, developed with a diazo solution, containing 5.9 gr. of 2-(2-amino- CO-NH The following table gives the shades of a number 0 the present process:

f dyeings, prepared aecording to One molecular proportion of the Combined with one molecular proportion shad. dlazocompqund of: 2.3 hydlotynaphthoyl 2-(2-aminophenyl)-pseudoazlmino-a-B- Anilin. Scarlet. nashthalene.

o. B-naphthylamin. Blmsh rod. Do. Ortho-chloroenllln. Do. Do. Para-toluidin. Red. z-(3-aminophenyl)-pseudoazlmlno-a-pfi-naphthylamin. Scarlet. naBhthalene.

o. 5-phloro-ortho-toluldin. Red. Do. 4-chloro-ortho-anlaldln. Scarlet. Do. o-ohloro-ortho-anlsidin. Do. 2-(4'-amlnophenyl)-pseudoezlmlno-a'fia-naphthylamin. Dark garnet rod.

nnfihthalene.

0. B-naphthylamin. Do. Do. Para-phenetidin. Do. Do. Meta-chloroanilin. Do. Do. 1 VIc1Lt1a-to1ui%in.t 1 id Bari claretttedd Do. oro-ort oo u in. ar garne re 2-(3'-amlno-4-methyl-phenyl)-pseudoazimlnoa-naphthylarnin. Bluish red.

a-fl-naphthalene.

Do. B-naphthylamin. Do. Do. Ortho-anlsidin. Bluish scarlet. Do. Para-chloroanilin. Bluish red. Do. 4-chloroortho-anisldln. Do. 2-(aamino-bmethoxy-phenyl)-pseudoazunino- Meta-nitrenllln. Blulah mot rod.

PB-naphthalene.

Do. B-naphthylamin. Garnet red. Do. Para-anisidin. Dark claret red. Do. Meta-chloroanilln. Garnet red. Do. 5-chloro-ortho-toluidinu Do. 2-(2-amlno4' -methyl-phenyl)-pseudoaziminofl-naphthylamin. Red.

n-B-naphthalene.

Do. Meta-toluidin. Red. Do. 5-chloro-ortho-toluldln. Red. lfi-(y-aminMwhlorophenyl)-pseudoaziminou-nephthylamin. Red.

afi-nephthalene.

Do. Ortho-anisidin. Blulsh scarlet. Do. #chlolo-Ortho-anisidin. Red. 2-(4'-aminophenyl)-pseudoeziminobenzene. Meta-nitranilin. Beddish violet.

Do. a-nephthylamin. Blulsh dark garnet red.

5-ohloro-L2-anisidin.

Bluish garnet red.

Two molecular proportions of the diazocom pound of:

Combined with one molecular proportion 01 bis-2. 3-hydroxynaphthoyl Shade:

Brownish claret red.

2-(2'-amlnophenyl)-pseud0azimino--fl- Dianisidin.

naphthalene. 2-(3-amlno-4'-methylphenyl)-pseudoazimino' do. Reddish brown. a-fl-naphthalene. 2-(2-amino-4'-methylphenyl)-psendoazlmlnodo. Brownlsh claret red.

mil-naphthalene.

One molecular proportion of the tetrazo- Combined with two molecular proportions of shad. compound of: 2.3-l1ydroxynaphthoy 5-amino-2-(4-amino-phenyl)-pseudoazimlnon-nephthylamin. Garnet red.

Do. fl-naphthylamln. Dark garnet red. Do. o-chloro-B-toluldln. Garnet red.

As an example; the graphical formula, of next to the last example in the above table may be given as follows:

NQNQQ u n no (am-Nam @NH-Aw Now what we claim is: 1. As new compounds azodyestuifs, having probably the general formula:

in which formula X represents the residue of a pseudoaziminobody of the general formula Aryl-N I!I Aryl arid n is either 1 or 2, which dyestuffs are when dry scarlet red to black violet powders, soluble in sulfuric acid to a red, violet to blue solution, yielding on reduction with stannous chloride an aminopseudoaziminobody and an arylid of 1-amin0-2-hydr0xy-3- naphthoic acid, which dyestufi's are adarited for the production of valuable color la es, when mixed with the usual substrata, and dye when produced on the fiber, the ve e table fiber in scarlet red to dark violet sha es of an excellent fastness, especially to kier the fiber of the material.

In testimony, that we claim the foregoing as ourinvention, we have signed our names, this 31st day of August, 1925.

AUGUST LEOPOLD LASKA. ARTHUR ZITSCHER. 

